Fortune of Baldwin
by Moonstone Plus
Summary: Herman Baldwin stresses as he gets ready for his 'not-date' with his crush Bailey, who wishes he was someone else. However, as the night goes on, Bailey finds herself shocked by the teenage boy and gets won over.


**Fortune of Baldwin  
**Chapter One: "Herman Gets a Date"

**This is a remake of our story Not A Date.**

As he looked around his walk-in-robe, fifteen-year-old Herman Baldwin found himself wanting to scream in frustration as he tried to work out what would be the best outfit to wear. Every article of clothing just felt childish or try hard. He was finally getting a chance to take Bailey out on a date and he didn't want _anything _to ruin his chances. He had already spent a good twenty minutes throwing his underwear out of his draw looking for a pair that wouldn't embarrass him or look to _kiddie_. Settling finally on a pair of Black Calvin Klein boxer briefs that were a little _tighter _in order to show off his young bulge and ass.

His erect cock struggled to fit inside the tightness but Herman was still comfortable enough if it meant he looked so good.

He made sure they were comfortable enough despite the slight tightness as he didn't want to struggle if he did get to strip down to these in front of the beautiful girl. While he wasn't expecting anything more than maybe a kiss on the cheek if he was lucky, he would be lying to himself if he said that he wasn't dreaming that _more _would happen.

His first trial outfit was a complete no-go.

The young teen had pulled out his tux and had dressed up to the nine with a tux vest, a pocket square and cuffs. He whined the moment he finished doing up the buttons as it made him look like he was going to a wedding or a funeral. While he _wished _that he was marrying Bailey, they were way too young for him to be dressed up like this. It had been that no-go that led him to be screaming at his clothing like a mad man.

A scream that attracted a reclusive creature of the house. Creeping down the short hallway towards the sound, a creature so pale it blended with the walls stepped silently on the floorboards. Like a snake sensing its prey, Chance slipped into Herman's room with a sly smirk.

"Trouble dressing, Herman? I thought you were supposed to be the fashionable one," Chance's voice was teasing, but the smirk was killer. Herman glared at him and tried to cover up the tux so he wasn't embarrassing himself.

While he wanted to scream at his older brother, Herman found himself whining completely. "I am… but this is important!"

"Clearly," Looking up and down at the outfit, Chance chuckled. "Who died?"

"My chances with Bailey!" Herman groaned.

Chance made a face, "Oh Herman… We buried those years ago,"

The younger teen simply just poked his tongue out at him before whining once more and doing something that he had never imagined doing in his life. "Chance… you have to help me."

Taken aback that his little brother actually wanted help preparing for a date rather than making sure he knew as little as possible. Furrowing his brow, the blond boy stepped past Herman and entered the dark-haired boy's closet, looking around at the clothes. Almost twice the amount he owned, Herman's closet was a cute mix of jeans, stylish jackets and plain coloured t-shirts that drew his eyes. From behind, Chance could hear his little brother stripping out of the tux and blushed to know that Herman was going to be almost naked. Focusing on the clothes in front of him, Chance picked out a few different options he thought would go well. Remembering the rule not to wear black with colour and made sure that the shirts matched the shoes. Herman fit mid-tones, flowing well with his dark brown hair, but needed a pop of colour matching the fire in his eyes.

Chance laid the clothes over his arm and shoulders before picking out one of Herman's _many_ pairs of shoes. He even noticed his little brother still owned a pair of clown shoes, right next to those he used for dance classes. Both causing him to smile from the pranks they had pulled in those very shoes. Turning on his heel, he went over and placed the collection on Herman's bed before beginning to go through things and match up a few pairs, seeing what would look best. He turned around ready to present his best option: A pair of black-gray skinny jeans, a deep maroon overshirt to match Herman's same colour shoes and an adorable green jacket that tied the whole thing together. Something casual but also obvious that he planned this for a nice day out. Besides, this red was Bailey's favourite colour.

As he turned around, Chance's eyes widened as he stared at Herman only in his Calvin Klein boxer briefs.

"Damn Herm, aren't they a bit t-tight?" Chance gulped, as he fully took in the view of his younger brother. Which he noticed was showing off his little brother _perfectly_. Herman's hands were covering up his crotch but did nothing to hide his bubble butt from the older boy, whose mouth ran dry at the sight.

A bubble butt that until now Chance hadn't found himself thinking of, with the thoughts turning into a nervous gulp as he felt his cock throb from the view.

"Bailey will love this one." He added, presenting the clothes. "I-I'll turn away so you can get dressed…"

"W-Why? I'm in my undies… so it's okay," Herman returned, blushing a little himself when he saw the look on his older brother's face. A look that only got worse as Herman removed his hands from his bulge in order to grab the selected black skinny jeans. Blushing a little when he saw Chance's eyes on his young bulge until he had finally covered it up with the jeans.

'_Oh my gosh, he looks hungrier than Blake when we go to the pool!_' Herman bit his lip and his eyes widened. Breathing heavily, the young boy started to pull on the black jeans. With Chance whining a little at the loss of seeing Herman in just his boxer briefs.

Standing up straight and showing off his undefined but slightly muscular chest to his older brother, the shirtless teen reached out and grabbed the maroon shirt then pulled it on. Much to the annoyance of his brother who found himself noticing for the first time how attractive his little brother actually was and how him wearing all black was only _adding _to his overall good looks. Herman's cheeks tinged a little pinkier when he saw Chance's attention and quickly pulled on the maroon tee and the green jacket.

Wanting to get away from his older brother's quickly growing looks of desire. He slipped on the shoes quickly and moved his feet around.

"Does it look, um… good?" Herman chewed his lip.

"Y-Yeah, Bailey is going to _love it_!" Chance admitted, not wanting to admit that _he _was loving the view.

"Thanks for the, um, help." Herman responded, blushing.

Quick to grab some of his things, the fourteen-year-old boy rushed from his room in a blur of black, red and green. He leaped down the stairs two at a time just to avoid being trapped upstairs with his big brother for another moment. Something said that Chance wouldn't be able to hold off his urges for much longer; The deep look of arousal in his eyes was making Herman feel unsettled and in the mirror he could have sworn that Chance licked his lips. After convincing his mother to drive him over to Bailey's house, the nervous teenager made his way up the footpath and while hoping that his confusing older brother was right, pushed the doorbell. Nervously he waited the painstakingly long time for Bailey to even began heading for the door, with the door feeling like it was only opened an hour later when it was barely more than a couple of minutes.

Opening the door, Bailey raised an eyebrow while internally groaning at the fact this date was actually going to happen. "Herman. You came,"

"H-hi Bailey. You look nice," Herman said with a blush, despite the fact that she was wearing a loose pair of pyjamas and put zero effort into her outfit. Even the girl's hair was messy, the curls wild and all over the place. With the boy only finding her prettier since she had allowed him to see, unprepped.

"Could you, uh, just give me a moment?"

Without waiting for an answer, Bailey slipped back inside. She shot a quick text to a _different_ Baldwin not to come over since Herman actually got the nerves to go through with this pity date. Playing with her curls, Bailey pulled her shirt open and took a quick photo of her small perky tits that she sent off to the other boy, a little promise of what _he_ would get and Herman would miss out on. Sure, Herman was cute and all but he really lacked a few things that the girl enjoyed in a stud. With a groan that her _great _afternoon with the stud of the Baldwin family, Bailey came back and looked at the younger boy.

"I guess you should come in," Rolling her eyes a little, Bailey stepped aside for Herman to enter. At least he was cute in that outfit. "Come on, let's _just _get this out of the way…"

Herman grinned at the chance of spending time with the curly haired girl, even if she didn't seem overly interested in actually giving him a chance to woo her. He was going to take his wins however, since just being in her house watching a movie with her alone was an upgrade for the fourteen-year-old who normally would be ran off unless they were hanging out as a group with Chance and Dusty.

After giving the younger boy a look, Bailey started to drag him upstairs to watch some random movie that would hopefully bore them both to death and get Herman to leave with enough time to bring the good Baldwin over.

* * *

The teenagers quickly found themselves getting _bored _completely with the movie. With the teens wondering why anyone would have thought that this was a good movie to release to the general public when their were better horror flicks on Youtube, then whatever this was meant to be. They were considering turning it off and just getting on the web to surf for videos until something in the terrible film caught their attention and annoyance.

They saw the cute blonde lead making out with the lead zombie.

"Ugh, this is _sooo _fake! A cute girl like her wouldn't go for someone like him! He's a weirdo and a Zombie!" Herman whined. "He eats the brains of animals!"

"And look _hot _doing it… unlike you when doing _anything,_" Bailey muttered, the curly haired girl using the lead zombie's good looks as a way to insult the younger boy who had been crushing on her since Chance had introduced them. Looking lazily over at her childhood friend since the movie shifted into another lame little song focused on the blonde lead, the girl noticed his adorable little pouty face which caused her to giggle a little. It was far too easy to torture Herman just by paying _any_ other boy the slightest bit of attention.

"Hey! People say that I'm hot!" Herman pouted. "But why would she go for some loser like him!"

Bailey smirked at the teen's pout but didn't comment on the '_hot_' bit, instead focusing on the easier burn from the second bit.

"Just wait until you get a girlfriend, she will be able to answer why a girl would go out with a loser." Bailey teased, poking her tongue out the now heavily pouting boy. Something in her knew that if she leaned in closer, Herman would suddenly lean close to suck her tongue. He just wanted her that badly. "You're drooling, Herman."

He couldn't help but blush from being caught out.

Rolling her eyes, she laid back on the bed completely ignoring the movie. "I bet you wouldn't even know how to kiss a girl, would you?"

Rolling onto his side, Herman raised an eyebrow. "I've kissed a girl before,"

The movie was out of their minds by now, allowed to trail off in the background without either teenager actually listening to a single song or little pep talk the characters made. Bailey shifted up onto a pillow, lounging there with a confused expression. She lazily twirled a finger around in her curly hair while getting all nice and comfortable against the wooden backboard. Looking down at the boy lying there on his side, trying to read Herman's face but finding herself unable to tell if he was serious or not.

When would Herman Baldwin have kissed a girl? For as long as Bailey could remember he was crushing on her alone, acting like they were a faithful couple despite frequently expressing her disinterest.

However, now that the boy said this Bailey was a little jealous. Yet eager to know more about this mystery kiss.

"Uh huh, I'm sure you have. And who did you kiss?"

"A girl at summer camp," Herman said, propping himself up on an elbow. Furrowing his brow slightly to remember the details, "Her name was… Ariana. Some of us played spin the bottle and I got her; We only kissed once."

Bailey remembered this girl from photos, having seen her with Herman in photos before. Even from first glance Bailey didn't like her being so close to Herman but always used the excuse that they were such close friends that the boy had become like a little brother in need of protection. Never would the girl have admitted to jealousy until about now, when a wave of it washed over her just at the thought of those two sharing even a chaste kiss. Wondering why this had never been brought up before by _anyone_.

Seeing the look of displeasure on his crush's face confused Herman. Was she angry he betrayed her, or didn't believe a word of it?

"It was just a little kiss! I didn't even want to kiss her," That part was a lie. She didn't want to kiss him, but the boy's pride forgot that part.

Bailey wasn't listening as she pushed herself up from the pillow's comfort, getting to her knees and crawling across the bed. An awe-struck Herman allowed her to climb over his small body, with the girl's hands pinned on either side of his head. The two looked into each other's eyes, seeing the fire burning in their iris.

Silently she lowered down and her rose up, just enough for their lips to come together in a soft yet passionate kiss. Though taken by surprise, Herman melted into their first kiss. Their fiery eyes closed as the teenagers' kiss deepened slowly, with Bailey lying down on top of the boy and pinning him down. The young boy's arms wrapped around her waist, pulling Bailey in closer. Herman pushed up a little against her sweet glossy lips, running his small tongue against them.

Bailey opened her mouth just enough to let his tongue slip into her mouth. Letting him explore for a moment, feeling it wiggling around inside. Soon as their kiss got more heated she pinned his tongue and forced her way into his mouth.

"Mm…" Herman moaned as his crush's tongue took over his mouth.

However, the feeling didn't last too long as Bailey broke their kiss all of a sudden. His lips stayed open, staring at her.

"Woah… did that just happen?" He asked in a whisper, watching the girl licking her lips. "I thought you were going to kick me out."

Wanting to shut the young boy up, Bailey pressed their lips together for another kiss. Loving that the submissive lover boy melted into her kissing skills and let out a soft moan around her lips. Bailey played with Herman's dark hair, giving soft little tugs as their kiss continued for a few minutes before breaking.

"So forward…" Herman gulped.

"You've seen _nothing_ yet, Baldwin."

Following down the younger boy's smooth side with one hand, she finally noticed the maroon shirt with its black collar, knowing instantly that Chance picked this out. She was expecting a tux. Peppering kisses on the lips of a cute boy who needed his brother's help to pick out an outfit, she hooked a slender finger under his tee before beginning to push it up. Brushing against Herman's pale skin as she eased his adorable shirt off, sliding it over Herman's head and noticing that his body had gone a little stiff.

Bailey rolled her eyes then dropped the shirt on her floor. Cupping his cheek, she guided him into a soft kiss. "What's wrong, Hermie?"

Herman shook his head, doing his best to loosen up. He was lying on Bailey's bed, having just kissed the girl of his dreams and she had stripped his shirt off mere seconds ago. All of this was so surreal that it felt like a dream, unreal for the fifteen-year-old boy struggling to wrap his head around this all.

"Ye-yeah… Can, uh, can I remove this?" Gentle fingers picked at Bailey's black pyjama tee. "Just to be fair,"

The curly-haired girl nodded and leaned up enough for his fingers to hook into her shirt and start pulling it off. Surprisingly slowly, the fabric moved up her slim body to reveal the tanned olive skin underneath. The boy's cute eyes wide as she allowed him to strip her, gentle when the fabric bunched under her arms. Bailey leaned in and kisses Herman while raising her arms for him to pull the shirt off, only breaking the kiss for it to go over her head. Bailey kissed Herman lightly, waiting for him to touch her breasts.

Something to shake the boy to his core what that the olive-tan skinned girl wasn't wearing a bra. Exposing her large breasts and dark nipples to the younger boy, whose cheeks were burning brightly.

When he didn't touch them, the girl had to lean into Herman's ear. "_Touch them if you like,_"

As teeth sunk into his ear, Herman's shaking hands glided up Bailey's slim hips ever so carefully. Following up her curves until brushing against her breast when he paused to swallow his courage. After a few seconds he started moving, caressing Bailey's large breasts.

"Oh god…" Herman moaned, feeling his cock throb as her breasts squished in his hands.

The two softly moaned as Herman rolled the soft breasts in his small hands, running his thumbs over the small dark nubs. Bailey seemed to love that, with the olive-skinned girl arching upwards and releasing a little moan from the lightness of his touch. So used to boys that roughly grabbed her tits and sucked on her nipples with eagerness, some even running their teeth over the nubs. Meanwhile, Herman we so gentle and sweet with his touches that Bailey was really enjoying herself.

Grinding her hips Bailey pressed down on the cute boy's throbbing cock, pleasuring them both while he massaged her chest.

"Ba-Bailey… you're so beautiful," Herman said in a low voice, propping himself up as Bailey rose up. The young boy moved in to plant a soft kiss on her breast and then the other. "Are we, um, are we going to go further?"

Pressing her hips down hard on the young boy, Bailey cracked a sly grin. "What do you think, Hermie? Do you want to have sex with me, or that _other_ girl from camp?"

It didn't take two seconds for Herman to blurt out: "You!"

'_Damn right you do_,' Bailey smirked before rolling off the young boy, getting comfortable on the bed. She lifted her legs up then slid her pyjama bottoms down to leave her only in a pair of white lace panties. A view so hot that Herman felt like his underwear were about to be full of cum.

"Holy _shit_…" Herman squeaked.

Trailing a finger down the middle of her thin, sexy body the girl watched his eyes follow it down to her pussy. Bailey ran down along her wettening pussy, moaning loudly as she teased herself.

Getting onto his knees, Herman stared at her almost naked body in awe. Her perfect curvy hips making her form so enticing and round tits that were so soft that they could be mistaken for marshmallows. Long slender legs and just kept on going, but the boy's attention was really on her panties. Watching the finger running around her clit in small circles, moaning with Bailey while she pleasured herself. Without even realising it, Herman reached down and cupped his concealed cock with a sheepish sound of pleasure.

Then suddenly her free hand touched his pale chest. He flexed for the girl, fully defining his thin four-pack that had been etched into his body for years. Shuddering as the hand teased and massaged his sexy thin body, Herman was Bailey was biting her lip hungrily. Not that he knew she was comparing him to his sexy older cousin Blake, remembering the hunk's chiseled body compared to the cute studly body Herman had been mostly hiding.

"Need some help down here, or am I not allowed to touch?" Staring at her pussy, the young boy's cheeks burned brighter.

The girl simply nodded and moved her hand away. To her surprise, Herman grew a pair and slipped his hand inside her lace white panties to run his thin fingers along her crack. Teasing the wet lips and gently pushing down like he was about to finger her.

"I didn't think a pussy would be so warm, a-and wet." He mumbled, pushing a finger into her willing hole. Bailey bit her lip, fighting back a moan. "I want to hear you moan, beautiful…"

Giving what he wanted, Bailey stopped trying to hide her pleasure and simply moaned aloud. Feeling his finger pumping gently in and out, the thin digit pushing in to the knuckle before pulling all the way out. For a boy who didn't know what he was doing, Herman felt amazing. Spreading her legs open slightly to allow him to finger her deeper, Bailey suddenly felt another finger forcing its way into her tightness and whimpered.

Herman was still in disbelief as he pumped two fingers in and out of his crush. She was so hot and tight; Just thinking about it squeezing his cock almost brought on an orgasm. Completely oblivious to the hand moving down his abs and start to play with the button to his shorts.

"Oh fuck, Herman! Do it faster, this feels amazing!" Bailey cupped her large tit, rolling it around in her hand. "Get me nice and wet for your dick,"

Working his fingers at a faster speed, Herman finger fucked her nice and good. Meanwhile, his zipper was being pulled down to reveal his black Calvin Klein boxer briefs and erect five-inch cock hidden inside.

All of a sudden Bailey's fingers curled around the outlined shape to tease the boy knuckle deep in her pussy, giving his cute length a little squeeze so that Herman was moaning just as loudly as she was. Music to her ears, his shy moans filling her bedroom in a matter of seconds.

"I want to see it without these," Herman said before pulling his fingers out. He gently glided the panties down Bailey's slender tan legs and put them on his shirt; The white lace was absolutely soaked with her juices by now and some part of him was tempted to steal the pair. "Woah… y-you look even better nude, Bailey. Like, I've imagined this so much but the real thing? _Damn!_"

Blushing from his polite comments, Bailey rubbed the tip of his cock with her thumb. "Th-thank you Herman…"

Without another word the young boy got down and closer to the girl's sweet dark pussy, watching her clit twitching and drool with sweet juices. Watching with a keen interest, wondering just how girls actually worked.

"Would you mind me ea-eating you out, Bailey?"


End file.
